Benzyl Alcohol → 2-Benzyloxy-thiophene

HRID 2080096Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2080096
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.I[C:15]1[S:16][CH:17]=[CH:18][CH:19]=1.N1C=CC=CC=1>COCCOC.[Cu]Cl.C(OCC)(=O)C>[CH2:1]([O:8][C:15]1[S:16][CH:17]=[CH:18][CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

8

Edukt 4

HCID 244Benzyl AlcoholHCID 1049PyridineHCID 189212-IodothiopheneHCID 178418339Butyllithium

Produkt 1

HCID 231304642-Benzyloxy-thiopheneAusbeute 9,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 62652Cuprous chlorideKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of benzyl alcohol (3.45 mL, 33.3 mmol) in 1,2-dimethoxyethane (80 mL) was added n-butyl lithium (2.6M hexane solution, 13.5 mL, 33.3 mmol) dropwise, which was then stirred for 10 minutes. Copper(I) chloride (5210 mg, 49.45 mmol) was added thereto, followed by stirring for 10 minutes on an ice bath, then, it was stirred for 2.5 hours at room temperature. 2-Iodothiophene (4995 mg, 23.78 mmol) and pyridine 320 mL were further added, and the solution was stirred for 13 hours under reflux. Ethyl acetate was added to the reaction mixture, which was sequentially washed with 1N hydrochloric acid, an aqueous solution of sodium hydrogen sulfate and brine, dried over anhydrous magnesium sulfate, and then, concentrated in vacuo. The resulting residue was purified by silica gel chromatography (hexane-ethyl acetate), and the title compound (420 mg, 2.21 mmol, 9.5%) was obtained.

Aufarbeitung

  1. stirringby stirring for 10 minutes on an ice bath
  2. stirringit was stirred for 2.5 hours at room temperature
  3. stirringthe solution was stirred for 13 hours
  4. temperatureunder reflux
  5. washwas sequentially washed with 1N hydrochloric acid
  6. dry with materialan aqueous solution of sodium hydrogen sulfate and brine, dried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue was purified by silica gel chromatography (hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-f3b215a72000418faa8b9292b136bc77
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07932272B2

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